Reduction of the carbonyl group in oxygenated
benzomorphan1 affords the corresponding alcohol (2). This intermediate is then N-demethylated by means of
BrCN. Acylation with
cyclopropylcarbonyl chloride[6][7] gives the amide (3). The alcohol is then converted to the ether by treatment with
MeI and base (4). Treatment with
LiAlH4 serves to reduce the amide function. Cleavage of the phenolic ether by one of the standard schemes affords moxazocine (6).
^DE 2517220, Montzka TA, Matiskella JD, "9-Alkoxy-5-methyl-6,7-benzomophane, VerfahrenE zu ihrer Herstellung und sie enthaltende Mittel [9-Alkoxy-5-methyl-6,7-benzomophanes, processes for their preparation and compositions containing them]", published 1975-11-06, assigned to
Bristol-Myers Co.
^Montzka TA, Matiskella JD, Chem. Abstr. 84, 59832k (1976).